Réaction #607428

Équation de réaction

potassium iodide

(2Z)-(hydroxyimino)(phenyl)acetonitrile

4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride

caesium carbonate

→

(2Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)acetonitrile

Rendement 80.0%

Solvants

acetonitrile

DMF

Conditions de réaction

Traitement

1. 1
   AutreThe solvent was then evaporated
2. 2
   workup.DISSOLUTIONthe residue dissolved in EtOAc
3. 3
   Lavagesubsequently washed with H2O and brine
4. 4
   AutreAter separation
5. 5
   Séchagethe organic phase was dried over MgSO4
6. 6
   Concentrationthen concentrated
7. 7
   AutreThe residue was purified by chromatography on silica gel

Mode opératoire

To a solution of (2Z)-(hydroxyimino)(phenyl)acetonitrile (7.3 g, 49.95 mmol, 1 eq.) in 280 ml of acetonitrile and 30 ml of DMF, was added 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (11.09 g, 59.94 mmol, 1.2 eq.) followed by potassium iodide (829 mg, 4.99 mmol, 0.1 eq.) and caesium carbonate (39.06 g, 119.88 mmol, 2.4 eq.). The reaction was stirred overnight at room temperature. The solvent was then evaporated and the residue dissolved in EtOAc, subsequently washed with H2O and brine. Ater separation, the organic phase was dried over MgSO4 then concentrated. The residue was purified by chromatography on silica gel to give (2Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)acetonitrile (10.30 g, 80% yield, only 1 oxime isomer).

Source